


Dean and the Kinkiest Thing I Can Think Of

by Hatsonhamburgers



Series: My Destiel Bingo entries 2018! [5]
Category: Supernatural
Genre: All smut, Alternate Universe - Canon Divergence, Anal, Anal Fingering, Anal Fisting, Anal Play, Anal Plug, Anal Sex, Castiel/Dean Winchester in the Bunker, Coming Untouched, Dean makes a porn, Destiel Fan Fiction Bingo 5, M/M, Masturbation, Masturbation Interruptus, POV Dean Winchester, Plot What Plot/Porn Without Plot, Porn Watching, Prostate Massage, Stuffing, like 13 porn, several porn
Language: English
Status: Completed
Published: 2018-03-17
Updated: 2018-03-17
Packaged: 2019-04-03 16:36:49
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 8,077
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14000205
Author URL: https://archiveofourown.org/users/Hatsonhamburgers/pseuds/Hatsonhamburgers
Summary: Dean is alone in the bunker finally.  That means he can cut loose and enjoy his new favorite pastime (Obsession).





	Dean and the Kinkiest Thing I Can Think Of

**Author's Note:**

> Entry for FF Bingo 2018- The Kinkiest thing you can think of.
> 
> Honestly, I could think of other kinky things, in fact, my tumblr searches left me shook XD, but I was good with this one- it was still sorta kinda really hot. I put off posting this cause omg what have I done
> 
>  
> 
> WARNING: Unless you are a professional, do not attempt this at home. This is fiction. A world without rectal tears or anything dangerous. Be kind to your bootyhole. :*)

Dean was alone in the bunker.

And that meant only one thing: fucking himself on anything he could find to put up his ass.

It had started a few months ago when Dean was feeling particularly horny after a hunting trip with Cas, and it had been too long since he’d ventured into town to pick up a woman, so he decided internet porn was on the menu. If he was being honest with himself, women in bars no longer did it for him. He felt too old- the girls in their 20’s made him cringe- all he could think about was what had happened to them in their lives that they though fucking an old dude like him would make them happy. And the older women never bought any of his bullshit pickup lines. It was just easier to stay home and jerk off. 

So he’d opened up the ol’ laptop and cruised around on Pornhub and tried to find something that interested him. He had clicked on a link that said, ‘Busty Blonde pegs Butch Boy’. He had no idea what any of that meant (except ‘busty’), so he clicked it and sat with his jaw unhinged as he watched a fit- looking man bent over a couch arm get fucked in the ass by a hot blonde woman with a strap-on. The attached dildo wasn’t enormous or anything, but by how it sounded, the guy really really liked it. Dean had looked down at his dick and was surprised to see he was getting hard watching something go in the guy’s ass. He was a little weirded out, so after watching the whole thing twice, he let go of his lubed-up cock long enough to click backwards to find something else. Of course, watching the video twice fucked up his algorithm, and there was all sorts of kinky shit on the suggested videos. Curiosity killing the cat and whatnot, he clicked on another pegging one where the woman was wearing a larger dildo really pounding into a dude, the camera angle moving around to show the vast quantity of come shooting out of the guy when she started jerking him off. That had peaked his interest. Was it possible to just get off from anal stimulation? He only sexual experience involving his usually ‘exit only’ policy had been with Rhonda Hurley in high school when she’d put him in pink panties, blew him and stuck a finger up there. It had felt weird, but man, if she got off on it, he was more than willing to do anything she wanted- her blow jobs were legendary. 

He had watched a few more pegging videos that night, coming so hard he saw stars. So of course, the next time he had time on his hands, he just clicked on whatever was in ‘suggested videos’ on his page. 

Which is how he saw his first object insertion video.

It was a beautiful blond dude with a shaved chest and clipped pubic hair and a really big dick, fucking himself with a cucumber. Dean had been flabbergasted. He watched in horror/fascination as the wide vegetable disappeared into the moaning guy’s hole, until the guy shot his load all over his chest, _without ever touching his cock_. Dean had looked down and realized he had just jerked it to a video with a serious lack of pussy.

He had shrugged and clicked on another. He managed to get off a second time that night, and was hooked.

It wasn’t long until he had decided to try it.

It was after a long and exhausting hunt in another state, one motel room for the three of them- getting a moment to jerk off in peace was impossible. They were all grumpy when they got back, and Dean had locked himself in his room right away, pulling open his laptop and finding the cucumber video again. He’d poured extra lube on his fingers and got a finger in his ass after a little relaxing and trying not to resist automatically. He had come so hard he could hear the blood pounding in his ears for several minutes and had stood on wobbly legs to his sink to clean up. He had been washing his hands when he spied his hairbrush laying there, thick black handle gleaming in the low light. He had picked it up, feeling the width of it and went back to his bed, still naked, and lubed up the brush, teasing his hole and stroking himself. He couldn’t really see what he was doing, so he turned on the camera on his laptop so he could watch himself. Seeing his hands and his shiny hole being teased by the brush handle was enough to get him turned on enough to relax his muscles and slide it in. The stretch hurt a little, but after watching his hand pump it in and out a few times, it felt like his hole was gobbling it up, sucking it in. It looked so naughty on the screen, just like one of the videos he’d watched so many times, so he put on a show for himself, pinching his nipples, moaning and fucking himself deeper with the handle. He had brushed a spot inside himself, setting off fireworks in front of his eyes, the spike of pleasure completely new to him. He’d come like a rocket in an matter of minutes. 

Of course, he’d been high on endorphins when he posted it. 

Dean had come down from his post-orgasmic bliss and panicked- but when he went to erase it, he saw it already had about a thousand hits! In a matter of minutes!

It wasn’t long before he had made several videos of himself fucking various items; a large carrot, the long tapered handle of the swiffer duster, a broom handle. He threw out every item he’d put in his ass, unable to stand the thought of his brother touching anything that had been up his butt. He had to take a special trip to Walmart to replace his brush, the broom and duster, and later a phillips head screwdriver, spatula, and small bottle of olive oil. His habit was getting expensive. Especially when he added the element of lace to the videos.

It was on that trip through the store that he’d suddenly had his eyes opened to all the thousands of things at Walmart that could fit up his ass, and the silky panties he could wear while doing it. 

It was in the automotive section where he got his idea for his next video. Sure, he felt a little guilty for shoplifting the black satin and lace panties, but he was a man on a mission to make a video, and the thought of thousands of orgasms around the world happening because of what he was doing, fueled his fire.

Then he had to wait until Sam and Cas went somewhere without him.

Cas had come across a ghost report in Muncie, Indiana, a milk run really, and Dean suggested they go and leave him behind so he could tune up Cas’s truck. They were so shocked that Dean would let them drive Baby without him that they practically ran out of the bunker.

Dean smiled. Too easy. 

He waited until Cas texted him that they were stopping for gas an hour later (and his responding text to remind him to use premium) when Dean went to his room and stripped down to nothing and pulled the panties on. He grabbed his laptop and headed for the garage.

Cas’s truck was old as hell, but there was something about the manliness of it and the era it was made that did something to Dean. He grabbed his socket set, turned on the tape player to Led Zeppelin’s _Whole Lotta Lovin’_ and sat his computer on top of a cart pointed at the front of the truck. He put his bottle of lube handy and laid a socket wrench, a new bottle of brake fluid with a long neck, and a rubber mallet with a long handle on a folded shop towel on the hood. He hit record and leaned over the hood spreading his legs and pulling the panties aside, using his slick fingers to rub circles on his entrance. It had been getting easier to put his fingers in as time went on, he figured it had to be muscle memory. Dean pushed both fingers in at once, moaning for effect, and looking back over his shoulder to watch himself on the computer screen. 

He had trouble with the angle, so he pulled his fingers out and climbed on the hood and laid back, knees up, spread wide, his cock displayed in the panties nicely, his asshole gleaming with slick when he pulled the thong aside. He gyrated his hips in time with the song, lifting his hips a little when he took the slicked-up handle of the socket wrench and pressed it to his opening.

He moaned and threw his head back as the hard metal breached his muscle. He loved how hard it was, how unlike flesh it felt, and pumped it in and out. The metal was smooth and went in deep easily, the coldness making him shiver. His cock throbbed in its confines, so he shifted it slightly so it peeked out of the top of the panties, but kept his hands off of it. 

After several pumps in and out, he removed the wrench and laid it back on shop towel beside him. He picked up the bottle of brake fluid and poured lube all over the top and neck, letting the lube drip onto his stomach and chest, making a show of rubbing it all over himself, his nipples, his belly button, and pushing it with his fingers into his hole. It was loose enough to take the slender bottle neck, so he worked it in, twisting it right and left, gasping loudly when it breached him, pushing it in hard and fast. He usually kept the videos under five minutes, so he needed to get to the large mallet handle soon. That and he was really itching to get it up his ass.

The plastic of the bottle was warmer and softer than the metal of the wrench, and the fluid inside splashed up the neck, creating a different sensation. Dean moaned and sped his hand up, biting his lip and pinching his nipples harshly. His cock was straining, and he pulled the panties down so the camera could see how he was leaking pre-come.

He withdrew the bottle and laid it with the wrench. He picked up the mallet and showed it to the camera, grabbing the lube and eyeing it. He rolled on his stomach and crawled the rest of the way up the hood on his knees, wiggling his lube-dripping asshole at the camera as he positioned the mallet in its head, the handle standing straight up. After a cursory swipe of lube, he rose to his knees and positioned his hole above the handle and slowly lowered himself onto it. He moaned and cried out as the blunt and wide handle pushed into him, the rubber feeling different from both the metal and plastic. It made him feel so full! He rode it in short thrusts, still not ready to come, considering turning around to face the laptop so the audience would see his cock when he came, when he spied something in the cab of the truck that made him pause. 

A wicked grin spread across his face. He pushed the mallet deeper, riding it faster, gripping the base of his cock to keep from coming. He stopped, rose off the mallet, pleased how stretched he felt, and slid off the hood and grabbed the laptop. He put the computer up on the hood, camera facing through the windshield. He grabbed the lube and opened the driver’s side door, and crawled in on his knees. The panties were soaked with lube and pre-come, so he pushed the front down below his balls, hooking them there. He stroked his cock a few times, winking at the camera. 

Dean faced the passenger door and straddled the gear shift knob and slowly began to descend over it with his clenching hole. 

The smooth top of the knob was worn down with use, and when it stretched him so much wider than the mallet handle, Dean cried out loudly. He imagined how Cas shifted when Dean taught him how to drive stick, and Dean closed his eyes and pictured Cas’s slender fingers made rough by hunting, and how they wrapped around the knob and caressed it, pulling it into gear, how they rested there between shifts, how his hand would absently stroke the shaft while he talked to Dean.

Of course, Dean started imagining Cas’s hand caressing his cock, touching it absently as he talked in Dean’s ear, squeezing when a gear needed to be changed. Dean pulled himself completely off the knob and turned so his back was to the laptop camera, so the view of his hole was more clear, and he watched over his shoulder on the screen as he lowered himself onto the knob again. His reddened hole stretched so slowly, opening as he pressed, popping over the knob part and squeezing shut over the handle. He could feel the round smoothness of the knob inside himself, and the way his rim clenched over the shaft. He pulled off all the way again, and pushed in once again, going deeper until he felt it press his prostate. He braced one hand on the backrest and faced the back of the truck, losing himself in the fantasy of Cas’s hand instead of his hand, and how the knob plundered him, pressing his prostate over and over. 

Then the knob became Cas’s fat cock, thrusting into Dean again and again, making his thighs shake and tremble. Dean let go of his cock, gripping the backrest with both hands and fucking down hard on the knob, going faster. He realized he was about to come, so he pulled off and turned again, facing the camera and pushing the knob in again, pressing his prostate firmly and gripping the dash with both hands, coming explosively, hitting the radio, the dashboard, the windshield. His ass rippled around the knob over and over, a shrill sound piercing the air. He realized he was screaming in ecstasy, and rolled his hips, causing another wave of pleasure to hit him, making his cock pump out two more spurts of come. In his thrall, the song had ended and it was silent in the cab as he had come, the only sounds were the sounds of sex, and moans falling from Dean’s lips as he came down. 

With a shaky finger, he clicked off Cas’s tape player before it finished changing sides. The silence was deafening. He slowly pulled off the knob, moaning again as the wide knob was pulled from his gaping hole. He took his fingers and felt his rim, sensitive and stretched, falling back onto the seat and propping his feet up on the dash, his cock and hole on display on the screen, showing his exhaustion. He watched his image as he fingered himself lazily, wondering if he had another one in him. He slipped in two fingers, then three easily, and managed to get his pinky in as well. It felt different, flesh inside him, softer and warmer. His cock hadn’t even completely deflated at that point, and it gave a twitch as he practically fisted himself. He just sat and watched himself, the squelching noise loud in the silence. 

His cocked jumped again. He was impressed he had enough energy left after all that for a second round. At that point, it was already twice as long as all the other videos he’d ever posted. He closed his eyes and twisted his hand, not quite able to get at his prostate at that angle. He imagined being held down, with someone else’s fingers inside him, a voice whispering in his ear, encouraging him, their stubble brushing his, catching, and blue eyes piercing his own. He moaned and finger fucked himself- it wasn’t enough, he needed more. His brain was so soupy that he couldn’t think of anything else to put in his ass. A dick. He laughed at himself, his fingers pushing in further. He wasn’t gay. He just had an anal fetish. And a pretty large gay following on the internet. But he’d never wanted a cock in his ass before.

He moaned and pinched his nipples, his mind wandering the length of the car, wondering if there was a jack handle in the truck. It wouldn’t be larger than the shift knob though. 

Then it clicked.

He pulled his fingers out, hopped out of the car, grabbed the laptop and wobbled on shaky, fucked-out legs to the tail of the truck. He sat the laptop on the ground, angling the camera up at himself. He reached out and touched the shiny massive globe of the trailer hitch with a slick finger. Definitely bigger than the shifter knob.

He poured lube from above over the clean shiny knob, letting it run to the ground. He dropped the bottle and straddled the hitch, back to the tailgate, hooking his elbows over the side so he could lower himself slowly. He spread his legs wide and squatted down, feeling the cold metal sooth his hot, worn-out hole. He gasped as he relaxed and increased pressure, the metal globe slowly stretching him unbelievably wide. He was sure he could do it- there was this guy he saw put a rolling pin in his ass, and this wasn’t nearly that big- and he moaned when his rim contracted around the far side of the ball, the hitch knob sitting comfortably inside him. He closed his eyes and unhooked one elbow to stroke his cock, only rotating his hips around until his found the right angle to press to his prostate. He forgot the camera as he closed his eyes and jerked himself faster. His other elbow slipped, and his full weight pressed the ball in harder, but he easily rested with the ball in his ass as he rolled his nipples in his fingers and pumped his fist. He kept his eyes closed, a vague image of a man swimming into his mind, kneeling in front of him, taking his cock into his mouth, sucking and fondling, then standing so he could push his cock in between Dean’s lips. Dean shouted and came as he imagined Cas looking down lovingly as Dean sucked him off. Dean’s ass spasmed around the trailer hitch in time with the come shooting from the tip of his cock, and he used the last of his strength to pull himself to stand, even as the orgasm continued, to pull himself off the globe, the burst of pleasure the pull on his rim created making him collapse on the floor, come all over his hands, cheek to the cool concrete, ass in the air. He flapped out an arm wildly to grab the laptop, yanking it toward himself and under his raised pelvis, hoping it was getting a shot of his over-stretched hole, still twitching, feeling ridiculously empty. 

He kind of dozed off in that position, waking when his back protested, spasming painfully. He shouted in agony and fell to the side. 

He couldn’t move. He laid there on his back, staring at the garage ceiling. Fuck. He strained to reach the laptop with his fingertips, the cold of the concrete starting to leak into his muscles as the sweat dired.

Fuck fuck _fuck!_

He pulled the laptop by his head and hit the spacebar to stop recording. An image of his close-up face flinching in agony as his back spasmed was frozen on the screen, and he would have laughed if he didn’t feel so much like crying. 

He could only awkwardly reach with one hand to close the video and check the battery. 14%. Fuck fuck fuck. 

He didn’t have enough battery to post or watch, but he had enough to email for help. 

Dean hoped he’d die on the floor instead. 

He thought about Sam finding him like that and leaving him and moving to Alaska.

He thought about Cas finding him-

Dean sucked in a breath. 

What the actual fuck was he thinking? He was obviously fucked up in the head. How could he do all that to Cas’s truck? It wasn’t like he could throw out the shifter knob or trailer hitch without Cas knowing something was up, let alone asking the angel to scrape him off the garage floor. What the fuck was he going to do?

His mind swirled around the images he’d just gotten off to; sucking Cas’s dick, getting fucked by him, holy shit.

Dean had always been a little weirdly attracted to Cas but damn. A few months of sticking things in his butt and suddenly he was gay for his best friend.

If he wanted to be honest with himself, there was nothing sudden about it. 

There was always things Cas was doing that had Dean going to his room and quickly looking at straight porn. Especially after hunting with the angel. Something about how they moved as a unit, reading each other’s minds, playing off each other’s looks, conquering as one. It didn’t work like that with anyone else, including Sam, and they were hunting together for years before Cas came along.

Dean lay there in a pool of his own come and lube, panties still stretched around his cock and balls, hole empty and clenching around nothing, back completely shot, and wondering what he was going to do about his newfound need to get fucked by his best friend.

Dean decided to bite the bullet and email Sam before his laptop battery died. 

He carefully opened it, and opened his gmail. He managed a _back is out, garage floor, don’t judge me, need help_ and then added, _don’t let Cas see me like this. Laptop about dead, phone in room_. He hit send and it chimed sent just as the computer died.

He sighed loudly, wincing as the movement made his back twinge. He turned his head slightly to look at the mess in the garage. There was the wrench, brake fluid bottle, and mallet on the hood of the truck covered in lube. There was the open door to the cab of the truck, come all over the cab, lube all over the shifter knob. There was lube dripping from the trailer hitch and dried come on the floor. And Dean himself, laying in the drying come, dressed in nothing but stained and ruined black lace panties, with the telltale bottle of half-empty lube just out of reach, and a laptop with all the evidence needed to convict him as a chronic pervert. 

He could at least try and get the panties off. Rather Sam find him completely nude than in women’s underwear. 

Dean tried and failed to lift his hips from the floor. He pulled his knees up slowly, one by one, until he could plant his feet on the floor. He felt a rush of lube dribble out of his ass onto the floor and rolled his eyes. He waited until he felt like his back was relaxed enough and used his fingertips to work the panties down his legs and off. He hooked them with one finger and brought them up to his face.

Ew. They were wrecked. He wadded them up and flung them as far as he could- he breathed a .sigh of relief as they slid under the Model T and into the shadows. He could throw them out later. 

All he had to do now was wait. He thought about jerking off to pass the time, but chastised himself- that’s how he got in that mess to begin with! He closed his eyes and let himself drift.

“Dean?” Sam’s incredulous voice jerked Dean awake. 

“Ow,” Dean responded as his back reminded him he was on the floor. It had to be a few hours later- he was freezing!

 

“What the actual- you know what? I don’t even want to know.” Sam’s footsteps drew closer. “Hold on, there’s coveralls over here…”

There were some noises and Sam came into view, holding a denim jumpsuit. Dean sighed, too tired to even feel bad about how this was probably traumatising his brother, and helped Sam get the jumpsuit on his legs and over his exposed crotch. Sam rolled him so he could get to his knees first then stand. 

They walked away from Dean’s crime scene and into the unknown. 

“What did you tell Cas?”

Sam started a little. “Uh, I told him to wait in the car, I’d forgotten something?”

“Jesus, Sam he’s not stupid,” Dean grumbled.

“Fuck, Dean, I just told him I’d forgotten the rock salt rounds. He seemed to buy it. But we need to hurry or-”

“Dean?” Cas was standing at the top of the steps to the garage.

“Oh Christ,” Dean whispered, closing his eyes, and feeling the blush creep across his face.

“Hey, Cas,” Sam said smoothly. “Will you get the rock salt rounds from the ammo room? Dean threw out his back working in the garage. I’m going to get him set up with painkillers and we can go again.”

“You sure you’ll be okay, Dean?” Cas had his head tilted in that way that used to make Dean think he was confused. He knew now that it was Cas reading the situation and sensing bullshit.

“Yeah, thanks man, I’m fine. Just wrenched something.” His blush flared brighter when he said ‘wrench’. 

Cas nodded and gave him a look. But he turned and walked down the hall to do as Sam asked.

Sam helped Dean to his room and deposited him on the bed. 

“Look, Dean-”

“Sam. I do not want to talk about this now, or ever, really, so just drop it, okay?”

“Okay, man, I’ll get your pills.”

Dean sighed, moving his pillow around until his head was comfortable. A few minutes passed and Sam came back with the pills. Dean took four and swallowed down a little water. He prayed he wouldn’t have to piss until they kicked in. What a fucking mess.

Dean’s exhaustion and the softness of the memory foam had him drifting off and into a deep sleep quickly.

 

****

Dean woke several hours later and rubbed his eyes. He slowly rolled and sat up. His back hardly protested and he breathed deeply. His back was so much better than it had been. Sometimes it was like that. A muscle spasm was unpredictable. 

He stretched carefully and looked around. It was 10pm, he’d slept most of the day away. He needed to get back downstairs to the garage and clean up his mess. Then charge his laptop. He glanced at his desk, freezing when he saw his laptop, already charging... and open. 

Fuck fuck fuck no.

He stood carefully and walked to the device, swiping a finger over the mouse pad and waking it up. 

A full screen still of his face frozen in bliss as he looked back to watch himself put two fingers in his ass while leaning over the hood of Cas’s truck met his eyes.

FUCK.

At least Sam had paused it before he got any further.

Dean slammed it shut and went to the closet to put on his robe. He needed a shower very badly but he first had to go destroy some evidence.

The garage light was still on when he went down the stairs carefully. There was a sound and he froze, his hunter instincts on high alert. He waited until he heard it again.

It was a soft moan. Low, followed by a sigh. Dean crept down the stairs. No one should be there, he’d looked and Baby’s keys weren’t on the table when he passed the war room.

There was a gasping noise, and Dean saw the top of a head of messy brown hair in the cab of Cas’s truck.

Oh my god. 

Dean should have left, should have gone and hidden in his room, but his stupid feet kept moving forward, determined to find out exactly what Cas was doing.

Dean peeked around the tool cabinet and got a clear view of the open driver’s side door. 

Cas’s coat and jacket were on the floor, his shirt unbuttoned, his hand wrapped around his cock, swiftly moving, stroking in a fluid, graceful motion. The light changed in the cab, and Dean realized Cas was watching something on his phone. 

_Cas was watching porn and getting off where Dean had shot his homemade porn._

Dean watched in amazement as Cas paused to prop the phone on the dash, the screen illuminating Cas’s face, sweat glinting in the low light. Dean’s hand crept under his robe, putting pressure on his erection. _Fuck,_ Cas looked so good like that. Dean inched closer. Cas was about to come by the look of it, and Dean wanted to see it happen. _Fuck_ , he wanted to catch it on his tongue. 

The thought made his dick twitch hard, poking out of his robe, like a dowsing rod toward the masturbating angel, and Dean swayed as the blood rushed away from his head.

Cas moaned louder, thrusting up into his hand. Dean was out in clear view now, and he saw that the tools had been put away and the come cleaned off the floor. The light in the truck brightened and Cas held up his free hand, pressing something to his nose and mouth, inhaling deeply. 

It was the ruined panties. Dean staggered into the tool cart, making about 4 screwdrivers fall with a deafening clatter.

Cas shot up, hitting his head on the door frame of the car as he twisted in his seat to see who was there. He froze, panties over his nose, his dilated eyes shiny and glazed, his hand still moving over his cock, too close to his orgasm to stop. His eyes widened as Dean strode closer, letting his robe fall open, revealing his cock, throbbing and already starting to leak. Cas’s eyes locked on his after sweeping over his body, and he released his cock gracefully just as Dean sank his lips over the silky flesh, arching his hips up as he came, the hotness of it hitting the back of Dean’s throat as he swallowed around Cas, sucking it down. Cas cried out, hands thrust into Dean’s hair, holding him still as Dean sucked the last few drops from Cas’s cock. 

Dean slowly pulled off, licking the tip a couple of times before looking up into Cas’s stunned eyes. They were dark with lust.

“Dean,” he whispered before pulling Dean onto his lap and kissing him, hard. Dean moaned into his mouth, shamelessly rubbing his cock on Cas’s deflating one. Cas thrust upward, licking down Dean’s neck, his hands roaming to squeeze Dean’s ass hard, grinding their hips together. Dean arched his back, and called out Cas’s name, lost in the feeling of the angel’s hands pulling the robe away until Dean was naked in Cas’s truck again, this time straddling him in the driver’s seat. Cas slid his hand down the length of Dean’s tailbone, pushing against his swollen asshole. Dean tried to spear himself on Cas’s fingers, but Cas pulled away. Dean looked down into Cas’s eyes, breathing hard. The phone behind him made a noise, and he turned to look at it. There on the screen was a close up of Dean’s asshole as he pushed nearly all four fingers into himself, right there on the seat of the truck they were sitting on. 

Dean whipped around and looked at Cas. 

“I brought you your laptop after Sam left.” A smile twitched at the corner of his mouth. “After I cleaned up a little, I thought I needed to see for myself what exactly you’d had done in my truck, Dean.”

Dean closed his eyes and shuddered. Cas’s voice was low and gravelly as always, but Dean could feel it in his cock, pressed up tightly to him.

“I played the video and decided to send it to my phone and watch it here. I hope you don’t mind.”

Dean shook his head slowly, his hips moving as lust pooled around in his groin. Cas thrust up, his now hard cock rubbing with Dean’s, making them both moan.

“Good, Dean. You look so fucking good on my truck, fucking yourself. The gear shift knob, that was something, very creative. The trailer hitch was the icing on the cake, really.”

“You’ve watched it all already?” Dean couldn’t stop rolling his hips, sneaking his hand to his own backside- he needed _something_ in his hole. Cas batted his hand away and used his own fingers to rub slow circles around Dean’s hole, pressing but not penetrating. 

“You’ve been asleep for eight hours, I had to do something to keep me busy.” He held up the panties. “These, Dean, I want to see you in them.”

Dean nodded, trying to grind on Cas’s fingers again, this time meeting with a little success when Cas’s middle finger breached his hole an inch. He sighed in relief. Cas grinned up at him.

“You like to be filled up, don’t you?”

Dean nodded and put their foreheads together, his eyes rolling shut as Cas’s finger slipped in further. It felt so different than Dean had expected. So real, so much more alive.

He moaned when Cas added a second finger, forgoing the lube. It was rough against his sensitive flesh. 

“I particularly like the hairbrush video. That’s been my favorite, until now, of course.”

Dean’s eyes popped open as he leaned back to stare at Cas in shock. “But I erased-”

“I’ve been following your Pornhub channel for a while, Dean.”

“Oh,” Dean wondered how long Cas had been jerking off to videos of Dean. His thoughts were cut short when Cas lifted him and slid him down onto his thick hard cock. Dean cried out. 

“Fuck!” Dean let Cas slowly push into him, the heat of his flesh bright inside of Dean, his every vein and wrinkle felt by Dean’s overworked tunnel. Cas thrust up into Dean until Dean relaxed into Cas’s arms, enjoying the fullness of it, so much more complete than anything he’d ever tried. 

Cas rolled his hips, sliding out and then back in. Dean moaned, meeting his next thrust. Soon Cas was pounding Dean down onto his cock, Dean limp and in ecstasy, crying out when Cas bit his nipple, pulling it with his teeth. Cas shifted Dean until he hit his prostate, sparking stars before his eyes. Cas hit that mark over and over until Dean was thrust over the edge, coming untouched between them, slicking their stomachs. Cas was thrusting in at a punishing pace, yanking down Dean’s head to kiss him deeply, coming hard in Dean, the hot liquid fiery inside him, dribbling out as Cas gave a few final thrusts. 

They sat there breathing hard together, Dean slumping over Cas comfortably, with the sound of Dean’s porn playing in the background. Dean giggled into Cas’s neck.

“I don’t think I want to post that one now,” he said, sitting up to look at Cas. 

Cas huffed a laugh. “Yeah, that one is just for me. But…”

Dean waited, his stomach fluttering hard as a slow smile crept across the angel’s kiss-bitten lips. 

“I can think of a few things we could post together.”

Dean shuddered. “Oh, god,” he muttered as he slumped back into Cas’s neck again, trying not to shift- he didn’t want Cas’s cock out of him just yet. Even as it softened, it just felt so good. “Yeah, let’s do...things.”

Cas chuckled and pulled Dean closer.

******

“The Bureau has been following similar crimes across state lines, so you can imagine we’d want to follow up on this.” Dean tried to hold as still as possible while the Sheriff nodded. He grabbed a file and handed it over to Dean. Cas stood serenely with his hands shoved in the pockets of his trench coat, nodding along. Dean tried not to let his eyes wander to Cas’s left hand settled in his pocket, where he clutched a small remote.

“Thanks Sheriff Riley,” Dean said, clenching his teeth as vibrations suddenly sped up against his prostate where the remote-controlled plug sat. “We’ll have these back to you this afternoon.”

Cas nodded professionally and seriously at the Sheriff and they walked out of his office.

“Fuck, Cas,” Dean whispered as they walked to the door of the station, “I can’t do this any longer, we need to go to the motel.”

Cas kept his face neutral as they walked. “Of course Dean. I have a surprise for you.”

Dean’s cock hardened impossibly more as they exited the station and headed to the Impala. He was grateful for his black wool pea coat- its length kept anyone from seeing his cock twitch in excitement, but the wool was burning him up. He pulled it off and threw it in the backseat, gingerly sitting down in the driver’s seat. The vibrations stopped. Dean slumped in his seat, the pressure on his prostate still there, but the overwhelming pleasure ceasing for a moment.

“You’re going to kill me,” Dean muttered, looking over at Cas as he started up his Baby and backed her out of the parking lot.

Cas grinned wickedly. That look always meant trouble.

The drive back to the motel was quick, and Dean shot Sam a text from the parking lot, telling him he would leave the file in Sam’s room and they were going to shower and nap before they met for dinner.

They had been getting two rooms for some time now.

Sam was enthusiastic that Cas and Dean had finally gotten together, but that’s as far as he wanted know about it. He had no clue how wild their sex life was, and he didn’t want to know. That was fine with Dean. 

The motel door slammed shut at the same time as the vibrating plug suddenly went ballistic. 

Dean fell to the floor, whimpering, on all fours, rocking back and forth as the plug punished his prostate. Cas moved around the room, the sound of clothing falling and the laptop opening mingling with the sounds pouring from Dean’s mouth.

Cas pulled Dean up and brought him over to the bed, facing him away from the laptop and yanking down the back of his still-buckled pants. Dean moaned when cool air hit his pink panty-clad ass, and he yelped when Cas’s hand landed a loud smack on the skin. Dean moaned as the thong was pushed to the side so the camera could see where it disappeared inside him. Cas showed the remote to the camera, the ping of comments filling the air from the live feed. Dean looked over his shoulder, just noticing how Cas was already naked, his hard cock bouncing as he positioned himself to Dean’s side, remote in hand, rising to his knees and brushing his erection over Dean’s reddened ass cheek. 

The vibrating slowed and Dean held still while Cas slowly worked the toy out of Dean’s hole. He whined when it was gone, feeling empty only for a moment until Cas pushed the tip of a much larger object into his asshole. Dean looked back and gasped as he was breached, laughing and moaning as the large purple plug was twisted back and forth until Cas worked it in past the enormous bulb and the flare sat snugly against Dean’s swollen entrance. He wiggled his hips, groaning as it nudged his prostate, and watched the screen as Cas unbuttoned Dean’s shirt and pulled it off him, unbuckled his belt and pulled his slacks down, lifting a leg at a time and letting Cas take his shoes and socks off as the pants were pulled off. Cas reached over and slapped Dean’s ass again, rubbing and squeezing his cheeks, massaging them and slapping them again. Dean spread his legs wider, his cock aching for release, soaking the panties. 

Cas was stroking himself languidly, watching Dean’s face on the computer screen, a small secretive smile on his face.

Dean loved this.

Cas crawled up the bed to Dean’s face, cock in hand, and grabbed Dean by the hair. Dean opened his mouth wide automatically, and was pleased to hear the laptop ping madly as Cas teased his lips with the tip of his cock, rubbing salty precome on his mouth like lipstick. Dean waited obediently as Cas worked, keeping his tongue in until he was told to lick.

“Lick it,” Cas commanded. Dean moaned and licked as Cas pushed his cock into Dean’s mouth, holding his head still by his hair, slowly pushing in, his hot flesh making Dean’s hole throb around the plug as it entered his throat. He relaxed his throat and took Cas further. Soon Cas was fucking Dean’s mouth, moaning and reaching back to rub Dean’s back and tap on the end of the plug. Sparks traveled up Dean’s spine at the contact. 

Cas pulled his cock from Dean’s mouth. “Are you ready?”

Dean nodded. Cas moved back to the plug and worked it out carefully, licking at Dean’s sensitive rim. The plug came out and was dropped on the bed. Dean fell on his stomach and was manhandled until Cas was between his legs, the laptop camera pointing at Dean’s open and spasming hole. Cas dipped fingers in, slapping Dean’s ass and pulling his cheeks apart to show their audience.

The comments pinged again. Cas pulled his fingers away and yanked Dean’s hips up again, rubbing the head of his cock over the clenching hole. Cas spit, the feel of it sliding down Dean’s crack making him shiver in anticipation, and he rubbed it in Dean’s hole with his cock, teasing and moaning. Dean whimpered a ‘please’ out, and Cas pushed in just the tip, then pulling it out with a pop. He pushed it in again, then pulled it back out, slapping Dean’s wet hole with his cock a few times. The laptop pinged madly. 

The teasing went on a little longer, then Cas pulled the pink panties down completely, yanking them off Dean’s legs. Cas laughed and Dean peeked back at him.

“What?” Dean mumbled.

“Hole-lover69 from Michigan wants me to stuff you.” Cas grinned down at him, wadding up the silk fabric.

“You kinky fucker,” Dean told the camera, reaching back to finger himself a little. Cas pushed his hand away, and started stuffing the panties into Dean’s ass, the rough of the lace and slickness of the soaked silk creating interesting sensations. ‘Oh, fuck, maybe this guy is onto something.”

Cas chuckled and reached under Dean to stroke his neglected cock. Dean cried out, the pleasure wracking his body as Cas pumped his fist and slowly pulled the panties from Dean’s hole and stuffing them in again with his fingers. Dean was practically wheezing from the pleasure, mumbling nonsense into the bed. He pushed up on his forearms so he could look under himself, watching the laptop through his and Cas’s parted thighs, watching the way Cas’s hand moved expertly over his cock. Fuck, it was so hot.

Dean’s orgasm was teetering on the edge, but he needed to come with Cas inside him. That was what Cas demanded of their performances, and Dean wanted to please him so badly. The comments were pinging like crazy at the panty trick, and Cas slapped Dean’s ass again.

“Ahh! Keep that up and you won’t be able to stuff your cock in me before I come!”

Cas dropped Dean’s cock, making him whimper and pulled the panties one last time from his hole. The fabric had soaked up all the lube and spit, so Cas tongued Dean a little for the camera, leaving him mostly dry. The computer pinged. 

“Some-like-it-red from North Dakota wants me to fuck you dry like this, what do you think, Dean?”

Cas only ever asked Dean first if he was unsure of something. The way it usually went was Cas read the comments and suggestions and did them to Dean. He liked being surprised more than anything, and trusted Cas to make him feel good. The audience of loyal followers loved it. 

“Do it!” Dean yelled, wiggling his hips. Dean rested on his elbows and looked over his shoulder at Cas, smiling as Cas faced away from the camera to spit onto his cock and spread it quickly. Dean trusted Ca’s judgement.

Even all the prep and toys and other random things being put in his ass, big things even, never really prepared him for how it felt when Cas thrust into him. His cock was heavy and big, bigger than Dean’s, and tapered at the root and fat in the middle. Cas slammed into him, making Dean fall onto his face. There was a pause as Cas moved the laptop under their spread thighs so the followers could see Cas fuck him fast and hard, the precome dripping from Dean as he was pushed to the edge.

“Fuck, oh yeah, baby right there! Fuck me harder! Yeah, make me come! Oh fuck!” Dean screamed as his orgasm exploded, his cock splattering release all over the screen of the laptop. Comments were flowing in, the pinging of comments under Dean fueling his pleasure. Cas hammered away, slamming into Dean’s prostate over and over until he shouted and filled Dean, pumping hot come into him. Slowly, Cas pulled all the way out, come still dripping from him, and pushed it back in. Dean felt him pull out and gather the come with the tip of his dick and try to push it all back inside him. Dean was floating. He felt Cas pull away and move the laptop, talking to the camera.

“Thanks for joining us, but we’re going to take a nap now, so signing off until next time.” Dean felt Cas lean in and kiss his puckered and well-fucked hole, his usual signature sign off (Dean had no idea where he got the idea from, but he kind of loved it).

Cas closed the laptop and rolled Dean over, kissing him deeply and caressing his face. “You want to get in the shower now of after our nap, Dean?”

Dean smiled sleepily at him. “What do you think?”

Cas chuckled. “I think that was our best video ever.”

“Better than the ‘Tossing a Salad with Fresh Vegetables’ one?”

“Less messy, I suppose, and I do enjoy the live interaction with our followers. It’s so nice that they enjoy our lovemaking.”

Dean snorted and giggled. “Come here,” Dean smiled and pulled Cas close, flipping the blanket over both of them. “Only you could call the kinky shit we do to each other in bed ‘lovemaking’.”

Cas smiled back at him. “Only because you love me so much.”

“That’s true,” Dean said, kissing Cas on the nose. “And you love me so fucking much. You are a very lucky man, really.”

Cas snuggled closer to Dean, tucking the hunter’s head under his chin. “Luck has nothing to do with it, Dean Winchester. I have what you called ‘mad skills’. I’m understanding this is a good thing to have.”

“Especially since your skills include doing amazing things to my ass, yeah, they are a good thing to have.”

Cas sat up a little. “Oh, I almost forgot,” he mumbled and he reached away from Dean somewhere. There was a rustling sound and Cas settled back into Dean, reaching down and pulling Dean’s legs apart. Dean felt a slick finger touch his hole. He shuddered and smiled into Cas’s chest as the angel slowly pushed the remote-controlled plug back into his hole, twisting it until it was comfortable. “We have another show tonight at 11. I have an idea pertaining to stealing a few things from the housekeeping cart and the white panties in your bag.”

Dean yawned and clenched around the plug, drifting off to sleep. “Sounds like fun.”

**Author's Note:**

> Seriously, I don't recommend anyone try this. Be safe, guys! :*)
> 
> A/N: If I die in a freak accident, please hack my account and erase this. I want my family to think I'm at least a little decent. Which I'm not XD


End file.
